تفاعل #95306

معادلة التفاعل

4-bromo-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

acetic acid

→

4-acetoxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONA mixture of 51.6 g
2. 2
   درجة الحرارةat reflux for 4.5 hours
3. 3
   درجة الحرارةThe mixture is cooled
4. 4
   أخرىsolids are removed by filtration
5. 5
   تركيزThe filtrate is concentrated
6. 6
   استخلاصextracted with hot hexane
7. 7
   غسيلThe extract is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
8. 8
   تجفيفdried over mangesium sulfate
9. 9
   تركيزconcentrated
10. 10
    أخرىto give an oil
11. 11
    workup.DISTILLATIONThe crude product is distilled at reduced pressure
12. 12
    أخرىto give a liquid, b.p. 152°-163° C. (0.01 mm)

الإجراء التجريبي

A mixture of 51.6 g. (0.137 moles) of crude 4-bromo-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one (Example 1274), 27 g. (0.162 moles) of silver acetate, and 200 ml. of glacial acetic acid is stirred at reflux for 4.5 hours. The mixture is cooled, and solids are removed by filtration. The filtrate is concentrated and extracted with hot hexane. The extract is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over mangesium sulfate, and concentrated to give an oil. The crude product is distilled at reduced pressure to give a liquid, b.p. 152°-163° C. (0.01 mm); λmax.MeOH =223 mμ (10700); νmax.=1745 (ester carbonyl groups), 1725 (ketone carbonyl groups), and 1235 cm-1 (acetoxy group).

المصدر